scholarly journals Stereocontrolled chiral synthesis of a trans-anti-trans tricycle by a transannular Diels–Alder reaction

1992 ◽  
Vol 70 (9) ◽  
pp. 2350-2364 ◽  
Author(s):  
Anne Marinier ◽  
Pierre Deslongchamps
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Synthesis ◽  
Diels Alder Reaction ◽  
Tricyclic Compound ◽  
Preliminary Study

The racemic and chiral synthesis of trans-cis-cis macrocyclic triene 5 is described. Heating this compound at 262 °C leads via a transannular Diels–Alder reaction to the tricyclic structure 6, which can be further transformed into tricyclic compound 7. This work constitutes a preliminary study for the synthesis of corticoids.

A chiral synthesis of (−)-cannabisativine: an application of the highly diastereo-selective hetero Diels-Alder reaction

1991 ◽  
Vol 32 (13) ◽  
pp. 1649-1652 ◽  
Author(s):  
Tatsuo Hamada ◽  
Tatsuya Zenkoh ◽  
Hiroki Sato ◽  
Osamu Yonemitsu
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Synthesis ◽  
Diels Alder Reaction

ChemInform Abstract: High-Pressure Mediated Asymmetric Diels-Alder Reaction of Chiral Sulfinylacrylate Derivatives and Its Application to Chiral Synthesis of (-)-COTC and (-)-Gabosine C.

ChemInform ◽  
2010 ◽  
Vol 33 (22) ◽  
pp. no-no
Author(s):  
Tamiko Takahashi ◽  
Yoko Yamakoshi ◽  
Kazuya Okayama ◽  
Junko Yamada ◽  
Wei-Ying Ge ◽  
...  
Keyword(s):  
High Pressure ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Synthesis ◽  
Diels Alder Reaction

scholarly journals Chiral Synthesis of Erythrina Alkaloids. I Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure.

1993 ◽  
Vol 41 (12) ◽  
pp. 2087-2095 ◽  
Author(s):  
Yoshisuke TSUDA ◽  
Shinzo HOSOI ◽  
Nobuya KATAGIRI ◽  
Chikara KANEKO ◽  
Takehiro SANO
Keyword(s):  
High Pressure ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Synthesis ◽  
Diels Alder Reaction ◽  
Erythrina Alkaloids

Chiral Synthesis of (+)-Methyl 5-epi-Shikimate by Asymmetric Diels-Alder Reaction of (S)s-3-(2-Pyridylsulfinyl)acrylate

Synthesis ◽  
1989 ◽  
Vol 1989 (03) ◽  
pp. 189-191 ◽  
Author(s):  
Tamiko Takahashi ◽  
Akira Lyobe ◽  
Yoshitsugu Arai ◽  
Toru Koizumi
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Synthesis ◽  
Diels Alder Reaction

Chiral synthesis of androsterone through intramolecular Diels-Alder reaction

1985 ◽  
Vol 50 (1) ◽  
pp. 144-145 ◽  
Author(s):  
Masataka Ihara ◽  
Izumi Sudow ◽  
Keiichiro Fukumoto ◽  
Tetsuji Kametani
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Synthesis ◽  
Diels Alder Reaction

High-Pressure Mediated Asymmetric Diels-Alder Reaction of Chiral Sulfinylacrylate Derivatives and Its Application to Chiral Synthesis of (-)-COTC and (-)-Gabosine C

Heterocycles ◽  
2002 ◽  
Vol 56 (1-2) ◽  
pp. 209 ◽  
Author(s):  
Tamiko Takahashi ◽  
Yoko Yamakoshi ◽  
Kazuya Okayama ◽  
Junko Yamada ◽  
Wei-Ying Ge ◽  
...  
Keyword(s):  
High Pressure ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Synthesis ◽  
Diels Alder Reaction

A,B-Diheteropentalenes by a Tandem Intramolecular Diels-Alder/Reverse Diels-Alder Reaction Sequence. Application to the Synthesis of Thieno[3,4-b]furan

1995 ◽  
Vol 48 (3) ◽  
pp. 593 ◽  
Author(s):  
JH Buttery ◽  
J Moursounidis ◽  
D Wege
Keyword(s):  
Furan Ring ◽  
Alder Reaction ◽  
Ring System ◽  
Diels Alder ◽  
Coupling Constants ◽  
Reaction Sequence ◽  
Acetylenic Ester ◽  
Diels Alder Reaction ◽  
Tricyclic Compound ◽  
Hydrolysis Of

Alkylation of 2-furylmethanethiol (28) with propargyl chloride gave the thioether (22) which on methoxycarbonylation afforded the acetylenic ester (30). On heating, this material underwent an intramolecular Diels -Alder reaction to give the tricyclic compound (32). In the presence of 3,6- di (pyridin-2′-yl)-s- tetrazine , (32) afforded methyl 4,6-dihydrothieno[3,4-b]furan-3-carboxylate (38) by a sequence involving a further Diels -Alder reaction followed by two reverse Diels-Alder reactions. The ester (38) could be dehydrogenated to give methyl thieno [3,4-b]furan-3-carboxylate (40) while hydrolysis of (38), followed by decarboxylation and dehydrogenation delivered the parent thieno [3,4-b]furan (5). 3-Methyl-4,6-dihydrothieno[3,4-b]furan (46) and 3-methylthieno[3,4-b]furan (47) were prepared; a comparison of the 4JMe-C=C-H coupling constants in the 1H n.m.r . spectra of (46) and (47) suggests that an increase in the C2-C3 furyl bond order accompanies the (46) → (47) conversion. Methyl 4,6-dihydrofuro[3,4-b]furan-3-carboxylate (39), 4,6-dihydrofuro[3,4-b]furan (27) and methyl 4,6-dihydro-6-phenylfuro[3,4-b]furan-3-carboxylate (53) were prepared by an analogous tandem reaction sequence. These compounds could not be dehydrogenated to the fully conjugated furo [3,4-b]furan ring system.

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